CA2776028C - Composes pyrrolo[2,3-d]pyrimidine - Google Patents
Composes pyrrolo[2,3-d]pyrimidine Download PDFInfo
- Publication number
- CA2776028C CA2776028C CA2776028A CA2776028A CA2776028C CA 2776028 C CA2776028 C CA 2776028C CA 2776028 A CA2776028 A CA 2776028A CA 2776028 A CA2776028 A CA 2776028A CA 2776028 C CA2776028 C CA 2776028C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrrolo
- pyrimidin
- trans
- cyclohexyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 263
- 108010024121 Janus Kinases Proteins 0.000 claims abstract description 58
- 102000015617 Janus Kinases Human genes 0.000 claims abstract description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- -1 cyano, phenyl Chemical group 0.000 claims description 245
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 190
- 229910052739 hydrogen Inorganic materials 0.000 claims description 188
- 239000001257 hydrogen Substances 0.000 claims description 188
- 150000003839 salts Chemical class 0.000 claims description 122
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 238000011282 treatment Methods 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 41
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 230000001404 mediated effect Effects 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
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- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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- 239000003937 drug carrier Substances 0.000 claims description 8
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 230000001363 autoimmune Effects 0.000 claims description 7
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 7
- IZXWMVPZODQBRB-UHFFFAOYSA-N piperidine-3,4-diol Chemical compound OC1CCNCC1O IZXWMVPZODQBRB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- YWEMBZPSYGFVOH-UHFFFAOYSA-N 3-methyl-4-(phenylmethoxycarbonylamino)benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)OCC1=CC=CC=C1 YWEMBZPSYGFVOH-UHFFFAOYSA-N 0.000 claims description 4
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- 208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
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- 150000002431 hydrogen Chemical group 0.000 claims 42
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne des composés pyrrolo[2,3-d]pyrimidine, leur utilisation comme inhibiteurs de la Janus Kinase (JAK), des compositions pharmaceutiques contenant les composés et leurs procédés de préparation.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25203909P | 2009-10-15 | 2009-10-15 | |
| US61/252,039 | 2009-10-15 | ||
| PCT/IB2010/054447 WO2011045702A1 (fr) | 2009-10-15 | 2010-10-01 | Composés pyrrolo[2,3-d]pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2776028A1 CA2776028A1 (fr) | 2011-04-21 |
| CA2776028C true CA2776028C (fr) | 2015-12-01 |
Family
ID=43413616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2776028A Expired - Fee Related CA2776028C (fr) | 2009-10-15 | 2010-10-01 | Composes pyrrolo[2,3-d]pyrimidine |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US8633206B2 (fr) |
| EP (1) | EP2488524B1 (fr) |
| JP (1) | JP5629324B2 (fr) |
| KR (1) | KR20120083452A (fr) |
| CN (1) | CN102574860A (fr) |
| AP (1) | AP2012006192A0 (fr) |
| AR (1) | AR078635A1 (fr) |
| AU (1) | AU2010308028A1 (fr) |
| CA (1) | CA2776028C (fr) |
| CL (1) | CL2012000795A1 (fr) |
| CO (1) | CO6531451A2 (fr) |
| CR (1) | CR20120164A (fr) |
| CU (1) | CU20120059A7 (fr) |
| DO (1) | DOP2012000080A (fr) |
| EA (1) | EA201290147A1 (fr) |
| EC (1) | ECSP12011855A (fr) |
| ES (1) | ES2426407T3 (fr) |
| IL (1) | IL218802A0 (fr) |
| IN (1) | IN2012DN02577A (fr) |
| MA (1) | MA33670B1 (fr) |
| MX (1) | MX2012004379A (fr) |
| NI (1) | NI201200053A (fr) |
| PE (1) | PE20121077A1 (fr) |
| TN (1) | TN2012000146A1 (fr) |
| TW (1) | TWI398444B (fr) |
| UY (1) | UY32947A (fr) |
| WO (1) | WO2011045702A1 (fr) |
| ZA (1) | ZA201202718B (fr) |
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| WO2010064146A2 (fr) | 2008-12-02 | 2010-06-10 | Chiralgen, Ltd. | Procédé pour la synthèse d’acides nucléiques modifiés par des atomes de phosphore |
| DK2411393T3 (da) | 2009-03-23 | 2014-04-07 | Glenmark Pharmaceuticals Sa | Kondenserede pyrimidin-dionderivater som TRPA1-modulatorer |
| ES2424341T3 (es) | 2009-03-23 | 2013-10-01 | Glenmark Pharmaceuticals S.A. | Derivados de furopirimidinadiona como moduladores de TRPA1 |
| KR101885383B1 (ko) | 2009-07-06 | 2018-08-03 | 웨이브 라이프 사이언시스 리미티드 | 신규한 핵산 프로드러그 및 그의 사용 방법 |
| TW201111385A (en) * | 2009-08-27 | 2011-04-01 | Biocryst Pharm Inc | Heterocyclic compounds as janus kinase inhibitors |
| ES2461967T3 (es) * | 2009-12-18 | 2014-05-21 | Pfizer Inc. | Compuestos de pirrolo[2,3-d]pirimidina |
| EP2620428B1 (fr) | 2010-09-24 | 2019-05-22 | Wave Life Sciences Ltd. | Groupe auxiliaire asymétrique |
| JP6128529B2 (ja) | 2011-07-19 | 2017-05-17 | ウェイブ ライフ サイエンシズ リミテッドＷａｖｅ Ｌｉｆｅ Ｓｃｉｅｎｃｅｓ Ｌｔｄ． | 官能化核酸の合成のための方法 |
| IN2014MN00228A (fr) | 2011-08-12 | 2015-09-25 | Nissan Chemical Ind Ltd | |
| DK2872485T3 (da) | 2012-07-13 | 2021-03-08 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| JP6453212B2 (ja) | 2012-07-13 | 2019-01-16 | ウェイブ ライフ サイエンシズ リミテッドＷａｖｅ Ｌｉｆｅ Ｓｃｉｅｎｃｅｓ Ｌｔｄ． | キラル制御 |
| CA2879066C (fr) | 2012-07-13 | 2019-08-13 | Shin Nippon Biomedical Laboratories, Ltd. | Adjuvant d'acide nucleique chiral |
| NZ703129A (en) * | 2012-07-17 | 2017-06-30 | Glaxosmithkline Intellectual Property (No 2) Ltd | Indolecarbonitriles as selective androgen receptor modulators |
| CN103896946B (zh) * | 2012-12-28 | 2018-04-03 | 浙江导明医药科技有限公司 | 用于预防及治疗多种自身免疫疾病的新化合物 |
| US20160123982A1 (en) | 2013-02-04 | 2016-05-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for assaying jak2 activity in red blood cells and uses thereof |
| EP2955181B1 (fr) | 2013-02-08 | 2019-10-30 | Nissan Chemical Corporation | Composé pyrrolopyridine tricyclique et inhibiteur de jak |
| JP6145179B2 (ja) * | 2013-02-22 | 2017-06-07 | ファイザー・インク | ヤヌス関連キナーゼ（ＪＡＫ）の阻害剤としてのピロロ［２，３−ｄ］ピリミジン誘導体 |
| DK2991988T3 (en) * | 2013-05-02 | 2017-08-21 | Hoffmann La Roche | Pyrrolo [2,3-d] pyrimidine derivatives as CB2 receptor agonists |
| WO2015108047A1 (fr) | 2014-01-15 | 2015-07-23 | 株式会社新日本科学 | Adjuvant d'acide nucléique chiral possédant une activité d'induction d'immunité, et activateur d'induction d'immunité |
| WO2015108046A1 (fr) | 2014-01-15 | 2015-07-23 | 株式会社新日本科学 | Adjuvant d'acide nucléique chiral ayant une activité anti-allergique, et agent anti-allergique |
| EP3095459A4 (fr) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Adjuvant d'acide nucléique chiral ayant un effet antitumoral et agent antitumoral |
| SG10201912897UA (en) | 2014-01-16 | 2020-02-27 | Wave Life Sciences Ltd | Chiral design |
| EP2924026A1 (fr) | 2014-03-28 | 2015-09-30 | Novartis Tiergesundheit AG | Aminosulfonylméthylcyclohexanes comme inhibiteurs de JAK |
| CN106459050B (zh) | 2014-05-14 | 2019-02-26 | 日产化学株式会社 | 三环化合物以及jak抑制剂 |
| WO2016024185A1 (fr) | 2014-08-12 | 2016-02-18 | Pfizer Inc. | Dérivés de pyrrolo[2,3-d]pyrimidine utiles pour inhiber la janus kinase |
| AU2017221193B2 (en) * | 2016-02-16 | 2019-03-14 | Zoetis Services Llc | Process for preparing 7H-pyrrolo (2, 3-d) pyrimidine compounds |
| CN107098908B (zh) * | 2016-02-23 | 2021-01-08 | 欣凯医药科技(上海)有限公司 | 一种吡咯并嘧啶类化合物的制备方法和应用 |
| WO2018167283A1 (fr) | 2017-03-17 | 2018-09-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés pour le diagnostic et le traitement d'un remodelage neuronal associé à un adénocarcinome canalaire pancréatique |
| EP3610264A1 (fr) | 2017-04-13 | 2020-02-19 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés de diagnostic et de traitement d'un adénocarcinome canalaire pancréatique |
| WO2020092015A1 (fr) | 2018-11-02 | 2020-05-07 | University Of Rochester | Atténuation thérapeutique d'une infection épithéliale |
| PL3915989T3 (pl) * | 2019-01-30 | 2023-12-11 | Felicamed Biotechnology Co., Ltd | Inhibitor jak i sposób jego otrzymywania |
| IL264854A (en) * | 2019-02-14 | 2020-08-31 | Bahat Anat | Spt5 inhibitors and methods of use thereof |
| WO2021003084A1 (fr) * | 2019-07-01 | 2021-01-07 | Ligang Qian | Antagonistes de p2x7r |
| CN114761011B (zh) * | 2019-08-26 | 2024-06-14 | 肯沃斯公司 | 用作jak1抑制剂的取代的(7h-吡咯并[2,3-d]嘧啶-4-基)氨基化合物 |
| CN115246833A (zh) * | 2021-04-27 | 2022-10-28 | 洛阳惠中兽药有限公司 | 一种奥拉替尼化合物及其中间体化合物的制备方法 |
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| CN1128800C (zh) | 1998-06-19 | 2003-11-26 | 辉瑞产品公司 | 吡咯并[2,3－d]嘧啶化合物及其组合物和用途 |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| TR200400105T4 (tr) | 1999-12-10 | 2004-02-23 | Prizer Products Inc. | Pirrolo [2,3-d] pirimidin bileşikleri |
| DZ3359A1 (fr) | 2000-06-26 | 2002-01-03 | Pfizer Prod Inc | DÉRIVÉS DE PYRROLO [2,3-d] PYRIMIDINE UTILES COMME AGENTS IMMUNOSUPPRESSEURS |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| BR0316470A (pt) | 2002-11-21 | 2005-10-11 | Pfizer Prod Inc | Derivados de 3-amino-piperadina e métodos de preparação |
| CA2536954C (fr) * | 2003-08-29 | 2012-11-27 | Exelixis, Inc. | Modulateurs c-kit et leurs procedes d'utilisation |
| CA2546192C (fr) | 2003-11-17 | 2010-04-06 | Pfizer Products Inc. | Composes de pyrrolopyrimidine utiles dans le traitement du cancer |
| RU2006135120A (ru) | 2004-03-05 | 2008-04-10 | Тайсо Фармасьютикал Ко. | Производные пирролопиримидина |
| CA2572331A1 (fr) * | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | Modulateurs de c-met et leur methode d'utilisation |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| JP5225079B2 (ja) | 2005-06-08 | 2013-07-03 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｊａｋ経路の阻害のための組成物および方法 |
| EP2251341A1 (fr) | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Hétérocycles inhibiteurs de Janus kinase-3 |
| AU2006273762A1 (en) | 2005-07-29 | 2007-02-01 | Pfizer Products Inc. | Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis |
| ES2401192T3 (es) | 2005-09-30 | 2013-04-17 | Vertex Pharmceuticals Incorporated | Deazapurinas útiles como inhibidores de janus cinasas |
| EP1951684B1 (fr) | 2005-11-01 | 2016-07-13 | TargeGen, Inc. | Inhibiteurs de kinase de type biaryl-méta-pyrimidine |
| EP1991532B1 (fr) | 2006-02-24 | 2017-01-11 | Rigel Pharmaceuticals, Inc. | Compositions et méthodes destinées à l'inhibition de la voie jak |
| CN101395134B (zh) * | 2006-03-02 | 2011-08-31 | 安斯泰来制药有限公司 | 17β-羟类固醇脱氢酶5型抑制剂 |
| WO2009049028A1 (fr) | 2007-10-09 | 2009-04-16 | Targegen Inc. | Composés de pyrrolopyrimidine et leur utilisation en tant qu'inhibiteurs des janus kinases |
| WO2009115084A2 (fr) | 2008-03-20 | 2009-09-24 | Schebo Biotech Ag | Nouveaux dérivés de pyrrolopyrimidine et leurs utilisations |
| PL2384326T3 (pl) * | 2008-08-20 | 2014-09-30 | Zoetis Services Llc | Związki pirolo[2,3-d]pirymidyonowe |
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- 2010-10-01 KR KR1020127012417A patent/KR20120083452A/ko not_active Application Discontinuation
- 2010-10-01 EA EA201290147A patent/EA201290147A1/ru unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102574860A (zh) | 2012-07-11 |
| ECSP12011855A (es) | 2012-06-29 |
| CL2012000795A1 (es) | 2012-09-07 |
| EA201290147A1 (ru) | 2012-11-30 |
| TW201125866A (en) | 2011-08-01 |
| US20110136765A1 (en) | 2011-06-09 |
| DOP2012000080A (es) | 2012-06-15 |
| MX2012004379A (es) | 2012-06-01 |
| TN2012000146A1 (fr) | 2013-09-19 |
| TWI398444B (zh) | 2013-06-11 |
| AR078635A1 (es) | 2011-11-23 |
| CA2776028A1 (fr) | 2011-04-21 |
| US8633206B2 (en) | 2014-01-21 |
| IN2012DN02577A (fr) | 2015-08-28 |
| ZA201202718B (en) | 2012-12-27 |
| CU20120059A7 (es) | 2012-06-29 |
| AP2012006192A0 (en) | 2012-04-30 |
| JP5629324B2 (ja) | 2014-11-19 |
| AU2010308028A1 (en) | 2012-04-19 |
| UY32947A (es) | 2011-05-31 |
| WO2011045702A1 (fr) | 2011-04-21 |
| ES2426407T3 (es) | 2013-10-23 |
| CR20120164A (es) | 2012-11-07 |
| CO6531451A2 (es) | 2012-09-28 |
| IL218802A0 (en) | 2012-06-28 |
| EP2488524B1 (fr) | 2013-07-03 |
| KR20120083452A (ko) | 2012-07-25 |
| EP2488524A1 (fr) | 2012-08-22 |
| PE20121077A1 (es) | 2012-08-10 |
| NI201200053A (es) | 2012-08-09 |
| MA33670B1 (fr) | 2012-10-01 |
| JP2013508266A (ja) | 2013-03-07 |
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